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Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Retro Mid-Century English Cottage

Just minutes to Keeneland and Red Mile. You’ll be glad you found this hidden gem in the Horse Capital of the World. Close to everything but in a safe and friendly neighborhood. Within ten minutes (or less) to Keeneland, Downtown, Rupp Arena, The Distillery District, UK, Masterson Station Park, Legacy Trail, The Arboretum or a scenic drive down Old Frankfort Pike. Our cozy cottage boasts two bedrooms with queen beds, a huge back yard with privacy fence to relax in, wi-fi, and large screen tv.

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 A cozy backyard cottage nestled in historic Pensacola Park, part of the national register of historic places. Conveniently, located along Hwy 27 (Nicholasville Road). A stones throw from the University of Kentucky, Kroger Field, 3 hospitals (Baptist Health, UK, and Children's Hospital), and Lexington's celebrated state botanical garden: The Arboretum. This standalone cottage features one dedicated parking space, full amenities, garden views, and artistic embellishments.

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

The Statesman / Walk to Rupp / Superb Deck

The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

The Rosewood Cottage of Lexington I Elegant & Cozy

Rosewood Cottage is one of Lexington's most unique and charming properties. Located steps away from Ashland Park and under 5 minutes to Downtown, this picturesque 1920's cottage offers history, charm and elegance in one extraordinary home. Relax with a bubble bath & champagne while reading a book from the host's curated collection, roast s'mores by the backyard firepit, or dive into some southern cooking in the newly renovated kitchen. This home away from home is not one to miss.